Theocritus’ Syrinx is one of the Technopaegnia, a corpus of Hellenistic and Roman calligrames with an intricate and enigmatic vocabulary. The Palaiologan scholars Maximos/Manuel Holobolos and John Pediasimos rediscovered this poem and composed commentaries for didactic purposes. The first part of this chapter delves deeper into the teaching of Holobolos, who has not received as much attention as other Palaiologan scholars. With a particular focus on his commentary on the Syrinx, it analyses Holobolos’ work on the Technopaegnia and addresses questions such as: Why was Holobolos interested in these poems? Which sources did he employ and how did he adapt them to his didactic needs? What literary competence did his students acquire by reading the Technopaegnia? The second part of the chapter explores Pediasimos’ detailed commentary on Theocritus’ Syrinx by addressing the same questions. It also deals with the scholarly context and dating of his exegetical work on the poem. The last part presents a comparative study to explore how Holobolos’ work influenced Pediasimos’ commentary. In this framework, the chapter also examines the manuscripts preserving the Technopaegnia in order to shed light on the scholarly milieu and production of these copies as well as the commentaries by Holobolos and Pediasimos.